Cl.[NH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:20])[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:6]=[CH:7][CH:8]=1.[Cl:21][C:22]1[N:27]=[C:26](Cl)[C:25]([Cl:29])=[CH:24][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:21][C:22]1[N:27]=[C:26]([NH:2][C:3]2[CH:4]=[C:5]([NH:9][C:10](=[O:20])[C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=3)[CH:6]=[CH:7][CH:8]=2)[C:25]([Cl:29])=[CH:24][N:23]=1To a solution of N-(3-aminophenyl)-3-nitrobenzamide hydrochloride (0.200 g, 0.681 mmol) and 2,4,5-trichloropyrimidine (0.071 mL, 0.619 mmol) in DMF (1.6 mL) was added potassium carbonate (0.30 g, 2.2 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous layer was extracted with EtOAc twice. The combined organics were washed with water, dried, filtered and concentrated to give the desired product as a light brown powder (330 mg). LCMS for C17H11Cl2N5O3 (M+H)+: m/z=403.9, 405.9, 407.9. 1H NMR (400 MHz, CD3OD): δ 8.82 (t, J=2.0 Hz, 1H), 8.45 (ddd, J=8.0, 2.0, 1.2 Hz, 1H), 8.34 (ddd, J=7.6, 2.0, 1.2 Hz, 1H), 8.24 (s, 1H), 7.97 (br, 2H), 7.76 (t, J=8.0 Hz, 1H), 7.56 (m, 1H), 7.43 (ddd, J=8.0, 2.0, 1.2, 1H).
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